


The Principal's Office

by konataizumi333



Category: Supernatural
Genre: Almost smut, Alternate Universe - High School, Alternate Universe - Modern Setting, Angst, Angstier than intended, BigBrother!Gabriel, Delinquent!Dean, Little bit of Fluff, M/M, Overprotective Gabriel, nerd!Castiel
Language: English
Status: Completed
Published: 2017-07-08
Updated: 2017-07-08
Packaged: 2018-10-24 18:04:51
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 2
Words: 8,873
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/10746984
Author URL: https://archiveofourown.org/users/konataizumi333/pseuds/konataizumi333
Summary: Dean and Castiel are both in the principal's office, but for very different reasons. Soon enough, they're dating, but Gabriel doesn't approve.Based on a Tumblr post.





	1. Chapter 1

**Author's Note:**

> Original Tumblr post:
> 
> One time in high school I was waiting to talk to the Vice Principal and this other kid came in and sat down next to me. He said "What are you in for?" And I said "Oh, they just want to know if it's cool if I miss my classes tomorrow to run sound and lights for a presentation in the auditorium. What are you in for?" and he said he stabbed a kid with a screwdriver. I told him we led very different lives and he agreed.
> 
>  
> 
> As soon as I saw this I thought Dean and Cas, so here it is.
> 
> My [tumblr](https://konataizumi333.tumblr.com/)

Castiel sat in the small waiting room in the office, waiting for the vice principal to finish talking with one of the teachers. He sighed, bouncing his leg as he looked around the room. A few chairs sat against the mostly plain walls. A few abstract paintings and potted plants were the only decorations. The receptionist smiled at him over the stacks of paper work sitting on the front desk.  
  
The door opened and a boy walked in and slumped into the seat next to Castiel, depositing his bag haphazardly in the chair on his other side. He was dressed in faded jeans, a black t-shirt, and a brown leather jacket that looked just a bit too big. His hair was artfully spiked in the front and light freckles covered his face. Castiel noticed that he was quite handsome, in a rugged sort of way. He was splayed out in the chair, leaning back with his legs stretched forward, a sharp juxtaposition to the way Castiel sat straight up in his chair with his hands in his lap.  
  
"So, what are you in for?" the boy asked with a grin.  
  
Castiel looked into the boy's green eyes, startled to hear him speak. "Oh, they just want to know if it's cool if I miss my classes tomorrow to run sound and lights for a presentation in the auditorium," Castiel replied before adding, "What are you here for?"  
  
"I stabbed a kid with a screwdriver," he answered casually.  
  
"Oh," Castiel said and looked forward again. "We lead very different lives."  
  
"Quite," the boy agreed.  
  
They sat there for another minutes before Castiel turned back to the boy. His curiosity was getting the better of him and he asked, "Why?"  
  
"Why what?" the boy asked, confused.  
  
"Why did you stab somebody with a screwdriver?" he clarified.  
  
"Oh," the boy said with a smirk. "He was being an asshole. I only wished I stabbed him sooner."

Castiel let out a huff of laughter at his carefree attitude, and the boy smiled as he watched out of the corner of his eyes.  
  
Another moment of silence. "Dean," the boy said, holding his hand out for a shake.  
  
"Castiel," he replied, shaking Dean's hand.  
  
Before either of them could say anymore, the principal's door opened and she popped her head out. "Dean Winchester," she called out tiredly before going back into her office.  
  
"Well, Cas, wish me luck," Dean said with a wink and a shit-eating grin. He got up and walked through the door. "Hey, Mrs. M, how are you? I-" Castiel heard before the door shut he was left alone in silence again.  
  
Before Castiel could sit too much longer the vice principal came in from the hall.

* * *

  
It was a full two months before Dean and Castiel spoke again. Castiel had started noticing Dean in the hallways ever since their encounter. He wasn't sure how he had never noticed him before because he appeared to be rather popular. He was always surrounded by a group of friends and Castiel learned that he had quite a bad boy reputation when he asked his friends about Dean.  
  
They met again much the same way they had the first time. Castiel was sitting in the office waiting room when Dean walked in. He smirked a bit when he noticed Castiel and sat down beside him.  
  
Castiel thought Dean was going to say something, but he remained silent, tapping out the rhythm of an unknown song on his leg. Finally, Castiel couldn’t take the silence much longer. “Did you hit someone with a hammer this time?” he teased.  
  
Dean looked over and chuckled. “So you remember me, huh?” he said flirtatiously.  
  
“Hard to forget,” he replied, making Dean smile more. It was true after all, you don't forget the person who stabbed someone with a screwdriver very easily, especially when said person was so handsome. It was possible that Castiel had developed somewhat of a crush on Dean in the past few months.  
  
“Well, in answer to your previous question, no. I did not attack anyone with any tools. Apparently skipping class is frowned upon,” he said matter-of-factly, causing Castiel to laugh. Dean examined him a moment longer with a small smile on his face. He turned away to rustle through bag and emerged a minute later with a sharpie. “Give me your hand,” he demanded.  
  
“What?” Castiel asked, confused.  
  
“Give me your hand,” he said slowly. Castiel narrowed his eyes, but offered up his hand anyway, not sensing any mal intent. He hoped.  
  
Dean grabbed his hand and pulled it forward, turning over and pushing up Castiel’s sleeve so that his wrist was bared. He pulled the cap off the marker with his teeth and wrote something on Castiel’s wrist, eyebrows furrowing in concentration. He released Castiel’s hand when he was done and recapped the marker, putting it away. The door to the principal’s office opened before Castiel could say anything and he heard Mrs. Mills call out, “Dean Winchester.”  
  
Dean looked up when he heard his name called. He turned back to Castiel with a grin. “That’s me,” he said with a wink before walking into the principal’s office. When he was out of sight, Castiel looked down at his wrist and was surprised to see Dean’s name scrawled messily next to a barely legible phone number. As soon as he realized what it was he blushed deeply, but smiled.

 

* * *

 

"What is that?" Gabriel demanded at dinner that night and reached out to grab Castiel's wrist.

"It's nothing, Gabe," Castiel insisted, pulling his wrist out of reach. He pulled his sleeve down, making sure all the writing was covered. Gabriel narrowed his eyes, but said nothing.

Castiel sighed. His parents' traveled around together for work, so oftentimes, they would be gone for weeks at a time. Their parents didn't want to be away so often, but they usually didn't have a choice, but despite the physical distance, Gabriel and Castiel were close with their parents. They called every night and skyped as often as possible, they made sure to always be home for holidays and birthdays and they always kept up with what was happening in their children's lives. And while Castiel wished his parents were home more often, he liked the arrangement, he felt a lot less pressure from his home life.

Most of the time. The rest of the time, there was Gabriel.

Unfortunately, due to his parents distance, Gabriel had become very protective of him, which Castiel appreciated because it meant he cared, but sometimes... sometimes it was too much. And he was sure that Gabriel would not approve of Dean's interest in him. So Castiel choose not to divulge that information.

He reached out for his glass of water, but it was too late when he realized his mistake. Gabriel's hand shot out and snatched his wrist, pulling it forward and sliding his sleeve out the way.

"Who is _Dean_?" he asked suspiciously.

"He's nobody," Castiel replied quickly, yanking his arm out of Gabriel's grip, putting his sleeve back in place, refusing to make eye contact with Gabriel.

"He's obviously not nobody, Cassie, his number is on your arm," Gabriel accused.

"He's just... just this guy from school," Castiel replied weakly.

"Mhmm." Gabriel stared at Castiel, who was steadfastly staring down at his plate. "Then why are you blushing?"

"I'm not blushing!" he exclaimed, raising his hands to his cheeks to make sure he wasn't.

"Why are getting all defensive if he's 'just a guy from school?'" Castiel looked up to see a victorious smirk on Gabriel's face before looking away again. "Come on, Cassie! You can talk to me. Do you like him?"

Castiel hesitated. He was never able to keep anything from Gabriel. "I... I don't know, maybe? We've only met twice and we've barely talked, so..." he trailed off.

"Were you planning you planning on using that number?"

Castiel looked at Gabriel, then looked down and started fiddling with his napkin. "Maybe."

"Ha! I knew it! You do like him!"

"I said I don't know!" Castiel protested, then in a quieter voice, "But... I want to see if maybe I do."

"So why are you being all shifty about it?" Gabriel asked, eyes narrowing again.

"I'm not being shifty," Castiel denied.

"Yes, you are," Gabriel said, concerned. "You won't look at me and- oh for heaven's sake, put that napkin down!" he snapped and Castiel looked down and noticed the napkin was crumpled and torn in places. He set the napkin back on the table and put his hands in his lap. But with nothing to distract his hands, he started bouncing his knee nervously. In a much less concerned tone, Gabriel shrewdly asked, "What are you hiding from me?"

"Nothing," Castiel answered quickly.

"Then look at me."

Castiel forced himself to look into Gabriel's eyes. "Nothing," he reiterated, but it sounded weak even to his own ears.

"Right," Gabriel stated. "You know, you've always been a crappy liar, Cassie. So. What. Are. You. Hiding. From. Me?"

Castiel stared back, not saying anything. Gabriel held his state a few seconds longer before letting out a dramatic sigh. "Fine!" They sat in silence a few minutes longer, tensing eating their dinner. Then Gabriel smiled like the cat that caught the canary. "So, how did you two meet?" he asked with an air of false casualness.

"What?" Castiel asked, going rigid.

"How did you and your boy toy meet, Cassie?" he asked innocently.

Castiel swallowed, knowing he had been caught. "I-I just, we... um..." he stuttered.

"Come on, spill the beans. And don't bother lying." Gabriel grinned wickedly.

Castiel huffed. "We meet a couple of months ago when I had to meet the vice principle about something," he blurted out.

Gabriel looked confused. "And you met because Dean was in the office... filling out forms? Helping the office ladies?" he asked, trying to figure out why it was such a big deal.

"Not exactly," Castiel mumbled, looking down at his plate.

Gabriel's face suddenly dawned with recognition and he gasped. "He was there because he was in trouble!" Gabriel exclaimed. "Cassie, I don't want you seeing this boy. He is trouble!"

"You don't even know what he was there for!" Castiel accused, sitting up in his seat.

"So what was he there for?" Gabriel asked flatly, with an eyebrow raised disapprovingly.

Castiel's anger vanished and he slumped in his seat, looking everywhere, but Gabriel's disapproving frown. "He... may have... kinda... stabbedakidwithascrewdriver," he let out in a rush.

"He what?" Gabriel asked, outraged. "Oh no. No, no, no, no, and, oh yeah, no! He's a delinquent!"

"You're a delinquent!"

"I am a respectable adult," he said with mock offense. Castiel just rolled his eyes. "He's violent."

"He's not violent."

"He stabbed a kid with a screwdriver!" Gabriel retorted, his voice going an octave higher than normal.

"Well, I know the kid who got stabbed and, quite frankly, he probably deserved it!"

I forbid you from seeing him."

"You can't do that!"

"Oh yes, I can."

"Gabriel, I appreciate your overprotectiveness because I know it means you care that much, but you can't stop me from dating someone," Castiel argued harshly.

"Sure I can."

"Oh yeah?"

"Yeah."

"And how, exactly, are you going to do that?"

Gabriel faltered. "I-I, well, I..."

"Exactly," Castiel said smugly, smiling in victory. "Maybe you could keep me under house arrest, but you can't prevent me from seeing him at school."

"I can homeschool you," Gabriel declared, but it was a weak argument. Castiel leveled him an unimpressed glare. "Fine!" Gabriel threw his hands in the air. "I can't stop you from being with him," he conceded. "But I don't have to like it."

Castiel smiled at his admission. "Of course not, Gabe. I never said you had to." Castiel watched as Gabriel glared at his green beans. "Truce?" he offered.

Gabriel continued to look down at his food with a look of contemplation, though Castiel knew he was putting on airs. Begrudgingly, he agreed. "Yeah, truce." He smiled. "For now."

"I wouldn't expect anything less," Castiel said with an answering smile.

Odds were that he and Dean wouldn't last long, and Gabriel would be right there with an "I told you so," but Castiel needed to make his own mistakes. He just hoped Gabriel could deal with it until then.

* * *

 

After dinner, in the solitude of his own room, Castiel sat on his bed, resting against the headboard. He had Dean's number typed into his phone and he was debating what to do. He decided he should text Dean, as a phone call would be to nerve-wracking, but he wasn't sure what to text. He decided to go simple.

_(8:46) Hello, Dean._  
_(8:46) This is Cas._

He sat, staring at his phone as he waited for a reply. Minutes ticked by and nothing happened. Castiel sighed. He was being foolish. Dean could be busy right now or not have his phone with him or something. There was no reason to feel so anxious.

Just as he stood up to grab a book, his phone pinged with a new message. He whipped around and reached for his phone too fast and he tripped and fell halfway onto the bed, then slid the rest of the way to the floor. He let out a huff at how stupid he was being and stood up and reached for his phone, slowly this time. He smiled as he read the message.

_(9:01) Hey, Cas_

**Notes for the Chapter:**

> Thank you for reading, comments and kudos are much appreciated. :)
> 
> I'm planning another chapter with more overprotective!Gabriel and a relationship between Cas and Dean, so look forward to it!


	2. Chapter 2

**Notes for the Chapter:**

> So...this turned out a lot longer and angstier than I originally planned. Also it became more about Castiel and Gabriel's relationship than Dean and Castiel's, but oh well.

"Aha!" Castiel startled awake at the sound of his door slamming open. He looked at the doorway with bleary eyes, but couldn't see anything because it was too dark. But then the lights flipped on and he quickly closed his eyes against the harsh brightness. He heard a groan and felt Dean shuffle behind him.

Castiel's eyes started adjusting to the light and he could barely make out Gabriel's figure before the blankets were flung off him and Dean, who was pressed against his back with his arms wrapped around Castiel's waist.

"Gabriel?" he asked, not awake enough to figure out what his brother was doing.

"You're... clothed." Gabriel asked, sounding confused and... disappointed?

Then it finally clicked in Castiel's sleep-addled brain. "Yes, Gabriel! Neither Dean nor I _sleep_ in the nude! Now get out!" he shouted. He didn't address the fact that he knew Gabriel expected to catch them having sex.

"Fine! You win this round. But I'm watching you," Gabriel warned before turning the lights off and backing out of the room, but not shutting the door, Castiel noticed.

Castiel slumped back against Dean, who held him tighter. "I'm sorry about him."

"Shh, it's okay, go back to sleep, Cas," Dean whispered in his ear sleepily.

Castiel settled down, but he couldn't sleep. After a few minutes, he heard Dean's breathing even out as resumed sleeping, but Cas was still awake, mulling over Gabriel's latest scheme.

It had only been two months, but Castiel and Dean's relationship was wonderful. Dean was wonderful. He was sweet and kind, despite his bad boy reputation. He held Castiel's hand in the hallway, he drove him to and from school. On their first date, he acted all shy and stuttery and he blushed whenever someone called them a couple. It was almost the opposite of what Castiel was expecting, but he loved it.

In other words, he was perfect. There were only two problems. First, was the fact that Dean wouldn't initiate anything physical beyond kisses—and mostly chaste kisses at that. Castiel wasn’t opposed to taking things slow, if that’s what Dean wanted, but he could tell the problem wasn’t Dean not wanting to do anything, the problem was that Dean didn’t think Castiel wanted to do anything. Which was wrong. So wrong.

Though it seems like an easy problem to fix, with the solution arose another problem.  All Castiel had to do was initiate something, but he was quite shy and could never work up the courage. He had thought Dean would try something so it wouldn’t be a problem, but apparently Dean was too much of a gentleman.

Basically, they were both waiting for each other to make the first move and Castiel knew it had to be him.

 _Stupid perfect boyfriend,_ he thought. He sighed to himself. Better to have someone giving him too much space than trying to force themselves on him he supposed.

The second problem, was Gabriel. 

Gabriel would probably be harder to deal with. Despite his supposed acceptance of their relationship, he was determined to dislike Dean. He was convinced Dean didn't really care for Castiel and was just having fun with him, and that Castiel would end up heartbroken. Castiel tried to convince his brother what a great guy Dean was, but Gabriel would have none of it.

At every opportunity, he tried to catch them doing inappropriate stuff so he would have evidence to back his claims, but he had yet to catch them doing anything (because they hadn’t done anything yet, but Gabriel just wouldn’t believe that).

And often, these two problems collided because just when Castiel thought he worked up enough courage to do something—Bam! There was Gabriel, ready to stop any “unseemly” acts.

But Castiel wasn’t ready to give up. 

 

* * *

 

 

The first time Castiel was able to get anywhere, was a Wednesday afternoon, when Gabriel had a late shift and wouldn’t be home until dinner time. Plenty of time to do what he wanted with Dean. 

They were sitting on the couch, Dean’s arm around him, watching tv. Castiel took a deep breath. Now or never.

Well, maybe not never, but it might be a while before he gets a chance like this again. 

He took another steadying breath and turned the tv off with the remote. He scooted so that he was facing Dean, who turned his head to face him with a questioning look. Castiel leaned forward, connecting his lips with Dean’s, but rather than pulling back like they usually did, Castiel wrapped one hand around the back of Dean’s neck, keeping him in place.

He could feel Dean hesitate at first, slightly confused, but he quickly got with the program, returning Castiel’s kiss, moving against his lips. He opened his mouth, inviting Castiel in. Castiel moaned at the warmth of Dean’s as their tongues moved together.

Dean put his arm around Castiel’s waist, encouraging to climb on his lap and he happily did so. Castiel could feel Dean’s half hard erection through his jeans and he could feel his own quickly hardening. He ground down, rubbing their erections together, causing them both to moan.

Dean pulled back from Castiel’s mouth. He started breathlessly, “Cas, wait—” but was interrupted as Castiel ground down again, making him gasp. He put a hand on Castiel’s chest, pushing him back and putting a few inches of space between them, though Castiel was still on his lap. “Hold on,” he said.

They sat there, both panting a little bit. “What?” Castiel complained.

“Cas, not that I’m against this,” Dean started, gesturing between the two of them, “but are you sure?”

“Yes, Dean. I am sure,” he stated.

“Are you sure you want this to progress further?” He asked carefully. “Because we can stop now if you want to.” 

Castiel rolled his eyes. “Dean, I initiated this, I’m pretty sure I know what I want,” he replied, slightly annoyed.  Secretly, he was pleased that Dean was so concerned about what he wanted, even if it was unnecessary.

“No, I know, Cas. But I just want to make sure you’re not just…trying to please me or something,” he said, looking earnestly into Castiel’s eyes.

Castiel smiled at that, reaching his hand up to gently stroke Dean’s cheek. “I appreciate your concern Dean, but I wouldn’t do anything I didn’t want to.” Of course, Castiel didn’t know that Dean thought they were just going to trade hand jobs or something, not go all the way.

Without giving Dean any time to respond, he attacked his mouth again, kissing him with an almost bruising force. There were no more complaints from Dean after that, and he seemed more enthusiastic now.

Dean started leaning back so that he was laying on the couch with Castiel on top. He ran his hands under Castiel’s shirt and across his back and Castiel shivered at the feeling of his warm hands.

Castiel started kissing his way along Dean’s jaw, down his neck, reveling in the way Dean shuddered against him. He reached down and started undoing Dean’s zipper, desperate for skin contact.

He had just reached under Dean’s under and grasped his cock, causing Dean to groan, when he heard a sharp thud. Followed by a much louder, “CASSIE!”

“Gabriel!” Castiel shouted, popping up so that he was sitting and looking over the couch. And there was Gabriel, frozen at the entrance of the living room, with a look of horror on his face, a box with the bakery’s logo on it on the floor.

Castiel groaned internally. Though he had moved his hand from Dean’s pants, from that position, Gabriel had probably seen exactly where his hand had been.

They were all silent and still for a minute, all waiting for someone else to make the first move. Finally, Gabriel seemed to regain some composure. Some. “What the hell?” he shrieked.

That seemed to break Dean and Castiel out of their trance and they leapt up off the couch, Dean hurrying to zip up his pants, both trying to straighten their clothes. Castiel tried to hold back a grimace as he looked at Dean. His lips were red and slightly swollen, his hair was messed up, and his clothes were rumpled. Castiel had no doubt he looked about the same.

There was another moment of awkwardness before Dean broke it. “Well, go to go, see you tomorrow, Cas,” he said hurriedly, placing a quick kiss on his cheek before walking towards the door. “Gabriel,” he said awkwardly with a nod as he passed him. It was silent except for the sound of the front door opening and closing, which seemed loud now and he couldn’t believe he didn’t hear it when Gabriel came in.

“You’re supposed to have the late shift tonight,” Castiel offered lamely, looking down, twiddling with the hem of his shirt.

In a calm voice, brought on more by shock than actually calm, he replied, “Pamela asked if I could cover her tomorrow if she would take my shift today.”

“Oh.”

“Oh? _Oh_? That’s all you have to say? Oh?” Gabriel practically shouted.

“Well what do you want me to say!” Castiel shouted back, suddenly filled with anger. “Yes. Dean and I were trying to have sex because I knew you wouldn’t be home. Is that what you want to hear?”

“But you _can’t_ , Cassie, not with him,” he pleaded.

“Why not?” Castiel was fed up with Gabriel.

“Because your first time should be special, with someone who cares about you. I know you’re young and eager to just do it, but you should wait for the right person,” Gabriel said earnestly.

Castiel scoffed. “You just don’t get it Gabriel. Dean _does_ care about me, and despite what you might think, he is the right person.” 

And with that, Castiel marched up to his room, leaving a slightly taken aback Gabriel in his wake. 

He slammed his door shut and curled up on his bed. He was just so… _frustrated._ Frustrated that Gabriel wouldn’t accept Dean. Dean was amazing. Castiel loved him, yes, love. What Gabriel said was true, his first time needed to be with the right person, and maybe a quickie on the couch before his older brother got home was not the way to do it, but it would be Dean. Castiel knew it.

 

* * *

 

 

The second time, was in the Impala, parked in front of Castiel’s house. It was dark out and Dean had just taken them out to dinner. 

Castiel was on his back in the front seat with Dean on top of him. He was working the buttons of Dean’s shirt open while Dean was trying to unhook his belt. It would’ve been perhaps a bit easier if they weren’t locked at the mouth, but neither seemed particularly bothered.

But then three wraps against the window made them stop. Dean glanced up then back down at Castiel. “It’s Gabriel.”

Castiel groaned and thumped his head back against the seat. They sat up and he turned and rolled down the window. “Did you need something, Gabriel?” Castiel asked through clenched teeth.

Gabriel had on a wide, and obviously fake, smile. “Just wanted to let you know that mom and dad are back and they can’t wait to see you,” he said with false cheer.

"It’s been a month since they’ve been home, I’m sure they can wait a few minutes longer,” he said pointedly.

“I don’t know, they’re pretty excited,” Gabriel said with a shit-eating grin.

“I’m sure it won’t be a problem.”

“Alright, then I’ll just wait here for you guys to finish up,” he said casually as he leaned against the side of the car.

“Fine,” Castiel spat and he rolled up the window.

He turned back to Dean and captured his lips in a rough kiss, fully intent on continuing. But Dean put his hand on Castiel’s shoulder and gently pushed him back. “Cas, no."

“Why not?” he asked petulantly.

“Cas. We are not going to do anything with your brother _right there._ ”

Castiel let out a frustrated sound. He realized he was probably being childish, but he didn’t really care at the moment. “But _why not_?”

“Because he’s your brother,” Dean said exasperated.

Castiel crossed his arms, signifying he would not leave, but Dean pointed him a stern look and he gave in. “Fine, fine. Not with my brother right there,” he conceded. He knew he wouldn’t have gone through with it anyway.

Dean smiled. “Good. Now go in and say hi to your parents who you haven’t seen in a month.”

“Yeah, yeah.” Castiel waved him off.

“Are you pouting?” Dean teased.

“I am _not_ pouting,” Castiel insisted, but Dean just chuckled.

“Sure,” he said placatingly. He leaned in and planted a gentle kiss before pulling back. “Now, go.”

Castiel tried to fight the smile that appeared whenever Dean was sweet. “Yeah. See you at school.”

He got out of the car and his smile immediately turned to a frown when he saw Gabriel smirk at him. They started walking towards the front door and Castiel tried to straighten his shirt.

“You know—”

“Shut up, Gabe,” Castiel snapped. Whatever Gabriel had to say, he didn’t want to hear. Especially anything that started in that sickeningly sweet tone of his.

He opened the front door and walked in to the kitchen where he was promptly assaulted with hugs from his parents.

“Castiel, I’m so happy to see you! I’ve missed you so much,” his mother gushed.

“It’s good to see you too, mom.” Despite his mood, he found it hard not to smile at seeing his parents again.  He always missed them when they were gone, and he often wished they could work locally so they could still live in the house, but Castiel had accepted their traveling and was determined to make the best of it whenever they were home. 

They had settled around the dining room table and his parents had just finished telling about their latest travels. “So, Castiel, how was your day? Gabriel said you were out with friends,” his mother asked.

Castiel looked at Gabriel who was avoiding his gaze. He narrowed his eyes, contemplating for a second. He and Gabriel had an unspoken agreement not to bring up Dean the last time his parents were home. Castiel, because the relationship was still new and he didn’t particularly want his mother sticking her nose in his love life, and Gabriel, because he was determined to get rid of Dean, so no sense in telling the parents if he wouldn’t be around long. How they avoided mention of Dean for the past two months of phone calls, skypes, and visits, Castiel wasn’t entirely sure.

But now the relationship felt more stable. And he wanted to vex Gabriel. And he really did want to share this with his parents. But also, you know, to vex Gabe. “Actually, I was out with my boyfriend.”

Everyone had a different reaction to the news.

Gabriel looked like he wanted to murder him, he could practically see the fire in his eyes. Castiel just sent him a small smirk before returning his attention to his parents.

His father choked on the water he was drinking and let out a weak, “Boyfriend?" 

His mother practically shrieked and her smile was so big it probably hurt. “You have a boyfriend, Cassie? How long has this been going on? Why haven’t you ever said anything? Oh my God, this is so exciting! What’s he like? Is he a good boyfriend?” she asked in a rush, hardly pausing for breath. 

Castiel chuckled at his mother’s reaction, but Gabriel just scoffed. Castiel sent him a dirty look. “Yes, mother. He’s wonderful. His name is Dean.”

“Oh, he sounds perfect,” his mother gushed, causing Castiel to laugh. “How long have you been dating?”

“Two months.”

“ _Two months_? And you didn’t tell us?” He would be worried his mother was angry, but her smile was too wide. His father had an uncomfortable smile, like he was happy for Castiel, just not really sure what to do.

“Well, I’ve just…been working up the courage.” It was only a half lie.

“Oh, you know you can tell us anything,” his mother said, looking concerned.

“No, I know, mom,” he hastened to reassure.  With the distance, it was actually a lot easier to tell his parents things rather than if they lived at the house full time. 

His mother smiled. “So, are we going to meet him?”

That gave Castiel pause. Was Dean ready to meet his parents? Was _he_ ready for Dean to meet his parents? Of course, he had met Dean’s family and everything went fine. He liked them and they liked him, so wasn’t it time for Dean to meet his? His parents were important to him, so of course Dean would have to meet them eventually, but what if they didn’t like him? Gabriel didn’t like Dean. What if his parents felt the same? What if Gabriel fed them lies and corrupted them. He looked at his mother and realized he had to answer.

“I don’t know, I hadn’t really thought about that. But, maybe?” he offered. He would talk to Dean about it later.

His mother giving him a knowing smile. “Well don’t fret too much, there’s no rush.”

He smiled at his mother, she always seemed to understand him. He turned to gage Gabriel’s reaction to all this. He was sneaking glares at Castiel and quite visibly fuming about the whole situation. Castiel shot him a smug look, causing Gabriel to narrow his eyes.

From there the conversation changed to safer topics, like school, work, the upcoming summer. 

It was late into the night when they all excused themselves to bed and Castiel’s father caught his arm before he could go upstairs. Castiel looked at his father in question, and he seemed to fidget. “Is, um, is everything alright with you and Gabe?” he asked.

Castiel sighed. Of course his parents had caught the discord between them. “It’s just…Gabriel doesn’t really approve of Dean and we’ve just been arguing about it.”

“Should I be concerned?”

“About Dean or Gabriel?”

“Both.”

“Probably not. I mean, of course not Dean, he’s great,” he rushed to assure, “but Gabe will get over it.”

His father studied him a few more seconds. “Alright. I trust you boys.”

Castiel smiled in relief. “Thanks. Goodnight, dad.”

“Goodnight, Castiel.”

In the privacy of his own room, he allowed himself to dwell on Gabriel a little longer.  He would never let anyone notice, but this thing between the two of them hurt him more than he let on. Because his parents were away so often, Gabriel was more than just his older brother. He’d never had many friends and he never felt the need to have more because Gabriel was always there. It had just been him and Gabriel for a long time and they had never fought like this.

Castiel just didn’t understand why Gabriel couldn’t accept Dean. Dean had never been anything but polite and kind around Gabriel and he had never done anything to warrant Gabriel’s behavior towards him. True, he wasn’t the most stellar student and had a knack for getting in trouble, but never for anything serious (except the screwdriver thing, but Castiel had learned that Dean rarely resorts to violence and Alastair had had it coming for a while), and he hadn’t affected Castiel’s performance in school.

He let out a shaky breath. Gabriel was important to him. But Dean was also important and Castiel wasn’t willing to give him up.  They were arguably the two of the most important people in his life and he just wanted them to get along and he wanted things with Gabriel to return to normal. 

Castiel had a fitful sleep that night.

 

* * *

 

 

Dean did meet his parents that weekend and they got along famously, much to the dismay of Gabriel and satisfaction of Castiel.

 

* * *

 

 

Two weeks later, Gabriel had to help out with an event at the bakery, so he would be out until the early hours of the morning. In other words, the perfect chance for him and Dean to finally get somewhere. 

Gabriel had barely agreed to go, knowing exactly what Castiel was thinking, but after multiple reassurances that Dean would be with his brother for their weekly brotherly-bonding-night, he finally left, shooting one last suspicious glance at Castiel.

Castiel had obviously lied about Dean. It was Friday and Dean spent Tuesday nights with Sam, but he must have been convincing for Gabriel to have actually believed him.

He hadn’t actually told Dean about his plans for sex, but he figured by telling him they would have the house to themselves, Dean could figure it out. And if not, he didn’t think Dean would have any complaints when their movie marathon turned to more interesting activities.

And so, three hours later, Castiel was in Dean’s lap on his bed, kissing him frantically, hands moving all over. Both boys had lost their shirt at some point and were exploring each other’s naked skin.

Castiel pulled back a bit to remove Dean’s belt, but they were still close enough that they were breathing each other’s air, panting heavily at the lack of oxygen. He was both excited and nervous as he started pulling on Dean’s zipper. He was hot and flushed, but in a good way, and achingly hard.

Finally, he worked Dean’s pants open and pulled them down a little. He rubbed Dean’s cock through his boxers, making him groan. His fingers toyed at the waistband, slipping under and grasping Dean’s hard cock. It was warm and firm in his hand as he started to jack Dean off.

“Cas, Christ–” Dean panted. He pulled Castiel down into a searing kiss with a hand tangled in Castiel’s hair.  He started to pull Castiel’s pants down as well, eager to touch.

“Dean, Dean,” he gasped as Dean freed him from his boxers. “I want– I want,”

“What do you want, Cas?” Dean asked breathlessly.

“I want you to fuck me.” He let out a moan as Dean thumbed over his slit, but then Dean paused as his words registered. 

Dean pulled at the hand currently on his dick, forcing Castiel to stop his ministrations. “Cas, I don’t know if that’s a good idea. You’ve never done it before,” Dean said, suddenly much more in control of himself.

“So?”

“So don’t you want your first time to be more…special?” Dean was looking at him, concern written in his features, and Castiel could feel his insides melt a little.

He sat back, creating more distance between them. “I want my first time to be with you, it will be special,” he said shyly.

Dean smiled at him. “Cas—”

"Dean,” he interrupted gently. “Just shut up, okay?”

Dean looked at him, then sighed. “Alright. But I promise you, I’m gonna make it special.”

Castiel smiled, thrilled. He leaned back in, capturing Dean’s lips, and they continued, but slower. Gentler, and more tender.

But then his door burst opened and there was Gabriel.

“Gabriel!” he shouted, pulling up the comforter in an attempt to cover himself and Dean.

“WHAT THE HELL!” Gabriel shouted, but he almost looked more hurt than angry. He took a deep breath, but it didn’t seem to help. “Hallway. Now!”

And with that he stomped out of the room. Castiel shot Dean a worried smile before scrambling up and tucking himself back in. The surprise had flagged his erection, so at least he wouldn’t have to face his brother with an awkward boner. “I’ll be right back,” he told Dean, who only gave him a reassuring smile. 

He walked towards Gabriel apprehensively, knowing it would be bad. Gabriel was currently facing away, but when he heard Castiel approach he whipped around with anger flaring in his eyes. “You lied to me, you said Dean wouldn’t be here,” he hissed.

Castiel didn’t have a good response, so he threw the question back at Gabriel. “You’re supposed to be at an event, what happened?”

“One of the ovens caught fire and they had to call the fire department, so they sent everyone home. Don’t deflect, Castiel, I know what was about to happen.” They were both whisper-shouting, as if Dean probably couldn’t hear every word.

“What do you expect, Gabriel? You were supposed to be away, it was the perfect opportunity,” he argued.

“I expect my little brother not to lie to me,” Gabriel snapped, and Castiel had to admit, that one stung a little. As a general rule, they didn’t really lie to one another so that they could always trust the other.

“Well, I didn’t have a choice!” he raised his voice, though it was still a whisper. It sounded kinda stupid, but switching to their normal voices would sound even stupider at that point.

“You did have a choice, Cas, and I think you made it. Him.” 

Castiel froze at that. He felt his blood run cold and tears prickle in his eyes. “Well fuck you!” he shouted. “Why does it have to be a goddamned choice? Why can’t I have both of you? What the hell is your problem with Dean?” Gabriel remained silent. “News flash, Gabe! I’m a healthy, horny, teenage boy and my boyfriend is fucking hot and yeah, I want to have sex with him. I didn’t realize it was a crime!”

“Cas—” Gabriel tried. He looked like he regretted what said, but it was too late.

“No! You know what? Fuck. Off. Alright? You don’t get any say in my life, so just fuck off,” he said hoarsely, barely holding back his tears. He turned and stomped back to his room, slamming the door behind him.

He collapsed to the ground, letting out a sob, then Dean was right there, scooping him into his arms. He sat back against the door with Castiel curled in his lap, head buried in the crook of Dean’s neck. He let out a shaky breath and couldn’t hold back the tears anymore. He let out racking sobs into Dean’s shoulder, all the while Dean stroked his back comfortingly, humming a song he didn’t know, but the vibrations were soothing just the same.

After a little while, he had calmed down and he wasn’t crying anymore, just sniffling loudly. Dean silently handed him a tissue, for which he was grateful. He had probably ruined Dean’s t-shirt, which Dean had put back on at some point while Castiel was outside, but Dean didn’t seem to mind. He slowly helped Castiel get to his feet and gently suggested, “Let’s go to bed.”

“Okay,” Castiel said quietly. He let Dean guide him to the bed and numbly got settled in with his face buried in Dean’s chest and Dean’s arms wrapped around him, holding him close. He thought he would have a fitful sleep, but with the exhaustion from the night’s events, he fell right asleep.

 

* * *

 

 

The next morning Castiel woke to the sound of Dean softly snoring. He had an arm thrown over his waist and his head was tucked into the crook of Castiel’s neck. 

Castiel laid still, not wanting to break the quiet peace of the morning just yet. He laid there, thinking of last nights’ events. His eyes welled up with tears, reliving the pain all over again, but he refused to cry again.

He couldn’t believe it. He couldn’t believe what Gabriel had said and he couldn’t believe what he said to Gabriel. They had had fights before, just like any brothers, but it had never been like this. Nothing had ever truly come between them. And Castiel didn’t know how to fix this other than leaving Dean, but he didn’t want to do that either. He knew he and Dean probably wouldn’t be together forever, that eventually they would break up, but was Castiel supposed to wait until then? It would probably be too late at that point anyway. 

His thoughts were interrupted when he felt Dean shuffle beside him. He rolled onto his back and let out a big yawn while stretching. He settled back down and looked at Castiel, blinking blearily at him. “Morning.”

“Good morning, Dean.”

Dean sat there staring a Castiel a few moments. “Are you alright?” he asked softly.

“I’m fine,” Castiel replied. Dean looked highly skeptical, but didn’t push. “I’m sorry about last night.”

“I’m not the one you should be apologizing to,” Dean responded. Castiel looked away from his knowing gaze.

"So how much did you hear?” Castiel asked.

“Just the stuff at the end, when you started shouting,” Dean said carefully. He looked at Castiel, waiting for him to say something more, but when Castiel remained silent, he sighed and looked to the ceiling. “Can I ask you something, Cas?”

“Of course.”

“Can you promise not to get mad?”

“Maybe,” Castiel replied warily.

Dean turned his head to look Castiel in the eye. “Do you want to have sex with me because you know it will make Gabriel mad?” 

He had not been expecting that. At first, he was mad that Dean might be questioning his motives. That Dean would think he would have sex without genuinely wanting it, but then he realized Dean might’ve been onto something. He thought about it for a moment.

“No,” he answered slowly. “I mean, like I said last night, I’m a horny teenage boy,” he said with a weak smile, “and I do want to go further with you. Sex isn’t something I take lightly and I wouldn’t do it if I didn’t want to. However, that being said, it is true that I might’ve been trying to rush it because I know Gabriel disapproves and that it would upset him.”

Dean nodded and turned his head back toward the ceiling. “Good, because I don’t want to do anything with you if you don’t actually want it.”

Castiel felt guilt at those words. He hadn’t really considered how Dean might feel. He had just assumed that Dean would be onboard with whatever. Dean had experience with both guys and girls, so Castiel believed that sex wasn’t a big deal to him, but maybe it was just as important to Dean as it was to Castiel.

“I’m sorry. I’m sorry I made you feel like I’m just using you against my brother, because I promise you I’m not. I really do like you, Dean,” he said earnestly, turning to his side to face Dean.

Dean turned over to face him as well. He smiled. “I know you do, Cas. And I like you too. Which is why I don’t want you to do anything that you’ll regret.” 

Castiel scooted closer, so that his face was buried in Dean’s chest, and he wrapped his arms around Dean’s waist. “You’re too good for me.” He heard Dean chuckle.

They laid in silence for a few minutes before Dean spoke again. “You know…I probably shouldn’t be telling you this, but I might have overheard Gabe on the phone a few days ago, and he said that he would be out of town two weeks from now. So…if you really want to do it, maybe we could plan to do it then.”

“Really?” Castiel asked hopefully.

Dean scooted back so he could look Castiel in the eye. “Yeah. It’ll be planned in advance, no interruptions, no surprises. It’s gonna be special.”

“Thank you.” Castiel cuddled closer into Dean’s warmth.

They laid like that a while, Castiel wasn’t quite sure how long, but eventually Dean looked at the clock. “Cas, as much as I would love to spend the day like this, unfortunately I have to go to work.”

Castiel groaned, not wanting to move, but he did. Dean worked part time at a garage owned by his father and uncle and he worked most weekends and some weekdays.

Dean went over to his bag and changed into some fresh clothes while Castiel sat on the bed watching him. When he was done, Dean walked back over and sat on the edge of the bed. “Hey, Cas? I want you to do something for me.”

“What is it, Dean?”

“Talk to Gabriel. Fix things.” Castiel rolled his eyes. “Hey.” Dean grabbed his chin, forcing Castiel to look at him. “Everything that happened? Don’t let it fester. Make things right. I know you’re mad right now, but you’re going to regret it if it gets worse, alright? So just take a little while to cool down and then talk it out.  Gabriel’s important to you, don’t let me come between you two.”

Castiel sighed, looking away. “Alright,” he replied quietly. 

Dean smiled. “Good.” He leaned forward and kissed Castiel on the forehead. “I’ll see you later,” he said, walking towards the door.

“Yeah, bye.” Castiel stared at the door after Dean left for a few seconds, then crawled back under the covers, pulling the blankets up to his chin. 

He knew Dean was right. He needed to talk to Gabriel, to figure things out. _But not yet,_ he thought. _Eventually, but not right now._

 

* * *

 

 

Nearly two weeks later and eventually had yet to come. Castiel knew he was being silly, but he just kept putting it off, telling himself that tomorrow would be the day, but chickening out when tomorrow came. 

He was scared. Scared that what had happened between him and Gabriel couldn’t be fixed. That he would have to choose between Gabriel and Dean, and he wasn’t sure who he would pick.

He was scared, but he was also mad. It was only a choice because Gabriel made it one, he wouldn’t let Castiel have both. It was all Gabriel’s fault.

And, Gabriel was keeping things from him. Dean had been right that Gabriel was going away for the weekend. Castiel had found some paperwork about a cake workshop that the bakery was sending Gabriel to. He was leaving tomorrow and he had yet to mention it. Probably so Castiel wouldn’t have time to make any plans with Dean.

Before everything with Dean, Castiel would’ve been the first to know about something like this. Gabriel would’ve been so excited coming home and telling him everything, even if it would be months before he’d leave.

But now, Castiel wouldn’t be surprised to wake up tomorrow and find a note on the counter saying he’d be back Monday.

So, for the past two weeks, Castiel had been avoiding him. Really, they had been avoiding each other. Gabriel tried to talk a few times in the first few days, but he was immediately shut down by Castiel, so he had given up. They spoke only when necessary, ate their meals separately, and pretended not to notice each other while avoiding eye contact when they passed.

So when Castiel came down for a glass of water and found Gabriel sitting at the dining room table, he didn’t expect Gabriel to try to speak to him.

“Cas, we need to talk.”

Castiel clenched his jaw. “I have nothing to say,” he replied, not looking at Gabriel.

“I know you know about my trip tomorrow.”

“How—”

“It doesn’t matter. Sit down. We need to talk,” he said forcefully, gesturing to the chair across from him.

Castiel debated internally for a moment. He huffed out a breath and sat down. “Fine.”

Gabriel let out a relieved sigh. “Okay, so, I’m not stupid. I know that while I’m away, it will be the perfect chance to finally have sex with Dean because, realistically, there’s nothing I can do to stop you. I’m sure you already have it planned out and everything.” He muttered the last bit angrily, more to himself than Castiel.

“What’s your point, Gabe?” he asked impatiently.

Gabriel took a deep breath. “I can’t stop you, so you have my consent.”

Castiel sat in shocked silence for a moment. “What?” he asked, slightly hysterical. “Your– Your consent?” He let out a laugh before his face turned murderous. “What the hell! After– After _all this_ , you just– just what? Consent?” he shouted, slamming his hands on the table and standing up.

“I thought that’s what you wanted!” Gabriel shouted back, confused and angry.

“I don’t want your consent because you don’t have another option,” Castiel said in a loud voice. He let out a shaky breath, then quietly, “I want you to be okay with it. You don’t have to love Dean, you don’t even have to like him, but you can’t hate him. I want you to approve because I really care about Dean, but I really care about you to. You’re my brother, Gabriel, and I don’t want to have to choose because I know I would choose you and I really don’t want to give up Dean.” His voice was raw by the time he finished and tears clouded his vision. 

Gabriel’s eyes were red as well at the end of his speech. “Oh, Cassie.” He hurried around the table and wrapped Castiel in a tight hug. Castiel returned the hug, gripping the back of Gabriel’s shirt tightly. It was silent while they stood like that, the only sound was the sniffling of both brothers.

After a few moments they pulled back and sat back down beside each other, wiping their eyes.

“I don’t want to make you choose, Cas. I’m sorry.”

Castiel sniffled. “Why don’t you like Dean?” he asked quietly.

“No, it’s– it’s not…It’s not Dean,” Gabriel said.

“What do you mean?”

“Cassie, I wouldn’t matter who you walked through that door with. You could come in here with a respectable, straight A, school president and I still wouldn’t approve. I’d still think you were too good for him. I know Dean’s a good guy and that he’ll take care of you, but I don’t want to give you up.”

Castiel smiled at Gabriel’s confession. “You don’t have to give me up, Gabe. You just have to share me,” he said.

“For now,” Gabriel said with a wry smile. “And about the whole sex thing, I know I’m probably overreacting, but it’s a big step and I don’t want you to regret it later.”

“I know how important it is and I wouldn’t do it if I wasn’t ready. Don’t you trust me?”

“Castiel, you are one of the most trustworthy people I know, of course I trust you. And despite the way I’ve acted, I trust Dean too,” he admitted reluctantly. “I know he’ll take good care of you.”

Castiel smiled. “Good.”

“Good,” he agreed.

“So, are we good now?” Castiel asked tentatively.

“Can I still be mean to Dean when he comes over?”

“Can I tell him what you said so he knows you don’t actually hate him?”

“But that’s no fun. He won’t be afraid of me,” Gabriel pouted. 

Castiel laughed. “He’s not afraid of you now.”

"Then apparently I’m not doing my job right,” he said, crossing his arms.

Castiel leaned over and drew Gabriel into another hug, knowing they would be okay.  “You’re a good big brother, Gabe.”

“Thanks.”

They both leaned back. “So, tell me about this cake workshop,” Castiel said, moving on to lighter topics. 

Gabriel grinned widely. “Well, apparently, when Pamela first heard about, I immediately popped into mind. So, she asked me if I wanted to go with her and obviously, I said yes, because, you know, cake. I never say no to cake.” Castiel smiled as he listened to Gabriel ramble on about all the cakes that he would get to eat that weekend. They would be just fine.

And now he could fully enjoy his weekend with Dean _without_ worrying about Gabriel.

**Notes for the Chapter:**

> Thank you for reading, comments and kudos are much appreciated. :)


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